- Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
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We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et3N).
- Vitale, Paola,Cicco, Luciana,Cellamare, Ilaria,Perna, Filippo M.,Salomone, Antonio,Capriati, Vito
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supporting information
p. 1915 - 1923
(2020/08/17)
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- Streamlined Routes to Phenacyl Azides and 2,5-Diarylpyrazines Enabled by Deep Eutectic Solvents
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A Deep Eutectic Solvent like choline chloride/glycerol (1:2 mol mol–1) proved to be an effective, sustainable reaction medium to easily synthesize both phenacyl azides and symmetrical 2,5-diarylpyrazines of interest in pharmacology and in coordination chemistry. Notable features of our report include: (i) nucleophilic substitution reactions of α-halo carbonyl compounds to the corresponding phenacyl azides compatible with the eutectic mixture, (ii) the reduction of phenacyl azides to α-amino carbonyl compounds, which undergo spontaneous dimerisation/cyclisation/aromatisation in the same eutectic mixture to provide valuable pyrazines. Telescoped, one-pot, two-steps stoichiometric/catalytic processes have also been successfully developed to furnish 2,5-diarylpyrazines in up to 95 % yield.
- Vitale, Paola,Cicco, Luciana,Messa, Francesco,Perna, Filippo Maria,Salomone, Antonio,Capriati, Vito
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p. 5557 - 5562
(2019/08/21)
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- Azido carbonyl compounds as DNA cleaving agents
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Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.
- Chowdhury, Nilanjana,Dutta, Sansa,Karthick,Anoop, Anakuthil,Dasgupta, Swagata,Pradeep Singh
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- Cyclization reaction of 2-azido-1-(2-hydroxyphenyl)ethanones with terminal alkynoates catalyzed by 4-dimethylaminopyridine (DMAP): Synthesis of 2-aminobenzofuran-3(2H)-one derivatives
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An unexpected cyclization reaction of 2-azido-1-(2-hydroxyphenyl)ethanones with terminal alkynoates catalyzed by 4-dimethylaminopyridine (DMAP) was developed, and 2-aminobenzofuran-3(2H)-one derivatives were obtained in moderate to good yields under mild
- Meng, Ling-Guo,Ge, Ni-Lin,Yang, Ming-Ming,Wang, Lei
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supporting information; experimental part
p. 3403 - 3406
(2011/09/12)
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